US1965072A - Manufacture of oxygen-containing aliphatic compounds - Google Patents
Manufacture of oxygen-containing aliphatic compounds Download PDFInfo
- Publication number
- US1965072A US1965072A US492361A US49236130A US1965072A US 1965072 A US1965072 A US 1965072A US 492361 A US492361 A US 492361A US 49236130 A US49236130 A US 49236130A US 1965072 A US1965072 A US 1965072A
- Authority
- US
- United States
- Prior art keywords
- zinc
- manufacture
- vapor
- steam
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title description 5
- 239000001301 oxygen Substances 0.000 title description 5
- 229910052760 oxygen Inorganic materials 0.000 title description 5
- 150000007824 aliphatic compounds Chemical class 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 26
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 23
- 239000011701 zinc Substances 0.000 description 23
- 229910052725 zinc Inorganic materials 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 235000019441 ethanol Nutrition 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- 229910052918 calcium silicate Inorganic materials 0.000 description 4
- 239000000378 calcium silicate Substances 0.000 description 4
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 4
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic primary alcohols Chemical class 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052571 earthenware Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229940043825 zinc carbonate Drugs 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
Definitions
- This invention relates to the production of ketones from aliphatic primary alcohols containing at least two carbon atoms, and especially to the production of acetone from ethyl alcohol.
- aliphatic ketones may be prepared in a highly satisfactory manner, by subjecting the vapors of the primary aliphatic alcohols, in admixture with water vapor, to the action of high or relatively high temperatures in the presence or" a catalyst mass comprising zinc, i. e. a catalyst mass containing zinc and/or one or more salts or compounds of zinc.
- the catalyst or catalyst mass may also advantageously contain one or more alkali or preferably earth alkali oxides, hydroxides or salts, such as carbonates or other salts and especially salts of the weaker acids, such for instance as silicates or borates.
- acetone can readily be produced from ethyl alcohol and homologous ketones can be produced from the homologous alcohols, e. g. diethyl ketone can readily be produced from propyl alcohol.
- catalysts suitable for use in performing the invention may be mentioned metallic zinc, zinc acetate, zinc oxide, zinc carbon-- ate; mixtures of two or more of such bodies; one or more of such bodies in admixture or association with one or more oxides, hydroxides or salts (e. g. carbonates, borates, silicates) of calcium, barium, magnesium or other earth alkali metals.
- metallic zinc, zinc acetate, zinc oxide, zinc carbon-- ate mixtures of two or more of such bodies; one or more of such bodies in admixture or association with one or more oxides, hydroxides or salts (e. g. carbonates, borates, silicates) of calcium, barium, magnesium or other earth alkali metals.
- the catalysts may, ii desired, be employed spread upon or deposited upon filling or contact materials, such for instance as pumice, kieselguhr or the like.
- the reaction of the invention may be performed at temperatures between about 200 700 C. and especially at temperatures between about 400-550" C.
- the reaction may be performed at any desired pressure whether higher or lower than normal atmospheric, for instance under reduced pressure or vacuum, or under higher pressures, such for instance as 3-10 atmospheres or more.
- I preferably employ mixtures of the alcohol vapor and steam containing relatively large amounts of steam or water vapor, e. g. amounts such as 2-10 or more times 'the volume of the alcohol vapor present.
- I may also mix with the alcohol vapor and water vapor, oxygen or a gaseous mixture containing the same, such for instance as air.
- I may mix oxygen or a gas containing the same 55 in a relatively large amount, such for instance as 25 times or more the volume of the alcohol vapor present, though it is, of course, to be understood that I may employ smaller quantities of such gases or operate in the absence of such gases.
- the mixture of alcohol vapor and water vapor may contain indifferent gases such for instance as nitrogen, carbon dioxide and the like.
- the mixture or" the alcohol vapor and water vapor, containing or not containing the gases or gaseous mixtures such as aforesaid, may be submitted to the reaction in any convenient way, as for instance the mixture may be passed in a rapid stream through a tube or other form of '7 apparatus (e. g. a tube or apparatus of copper, iron, staybrite, earthenware, or the like) filled or provided with a catalyst and heated to the desired temperature.
- a tube or other form of '7 apparatus e. g. a tube or apparatus of copper, iron, staybrite, earthenware, or the like
- Example A mixture of ethyl alcohol steam and oxygen in the proportions of 1:511 by volume is passed in a rapid stream over or in contact with the catalyst contained in a tube (e. g. of copper) and 'naintained at a temperature of between about 4'75 and 485 C.
- the catalyst is composed of zinc acetate or of zinc oxide and calcium silicate, e. g. a mixture of two molecular proportions of zinc oxide with one molecular proportion of calcium silicate.
- the resulting acetone can, if desired, be purifled by frictional distillation.
- Process for the manufacture of an aliphatic ketone which comprises subjecting the vapor of a primary aliphatic alcohol containing at least two carbon atoms to reaction with steam at an elevated temperature in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
- Process for the manufacture of an aliphatic ketone which comprises subjecting the vapor of a primary aliphatic alcohol containing at least two carbon atoms to reactionwith steam at a temperature between 200 and 700 C. in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
- Process for the manufacture of an aliphatic ketone which comprises subjecting a mixture of between 2 and 10 volumes of steam and 1 volume of the vapor of a primary aliphatic alcohol containing at least two carbon atoms to reaction at an elevated temperature in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
- Process for the manufacture of acetone which comprises subjecting the vapor of ethyl alcohol to reaction with steam at an elevated temperature in presence of a catalyst mass comprising essentially zinc and which is free from other heavy metals.
- Process for the manufacture of acetone which comprises subjecting the vapor of ethyl alcohol to reaction with steam at an elevated temperature in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
- Process for the manufacture of diethyl ketone which comprises subjecting the vapor of propyl alcohol to reaction with steam at an elevated temperature in presence of a catalyst mass comprising essentially zinc.
- Process for the manufacture of acetone which comprises subjecting the vapor of ethyl alcohol to reaction with steam at a temperature between 200 and 700 C. in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
- Process for the manufacture ofacetone which comprises subjecting the vapor of ethyl alcohol to reaction with steam at a temperature between 400 and 550 C in presence of a catalyst mass comprising essentially a. compound of zinc and a compound of an earth alkali metal.
- Process for the manufacture of acetone which comprises subjecting a mixture of between 2 and 10 volumes of steam and 1 volume of ethyl alcohol vapor to reaction at a temperature between 400 and 550 C. in presence of a catalyst mass comprising essentially a compound of zinc and a compound of an earth alkali metal.
- Process for the manufacture of diethyl ketone which comprises subjecting the vapor of propyl alcohol to reaction with steam at a temperature between 200 and 700 C. in presence of a catalyst mass comprising essentialy Zinc.
- Process for the manufacture of diethyl ketone which comprises subjecting the vapor of propyl alcohol to reaction with steam at a temperature between 400 and 550 C. in presence of a catalyst mass comprising essentially a compound of zinc and a compound of an earth alkali metal.
- Process for the manufacture of diethyl ketone which comprises subjecting a mixture of between 2 and 10 volumes of steam and 1 volume of propyl alcohol vapor to reaction at a tel perature between 400 and 550 C. in presence of a catalyst mass comprising essentially a compound of zinc and a compound of an earth alkali metal.
- Process for the manufacture or" acetone which comprises subjecting the vapor of ethyl alcohol to reaction with steam at a temperature between 400 and 550 C. in presence of a catalyst composed of zinc oxide and a compound of an earth alkali metal.
- Process for the manufacture of acetone which comprises subjecting the vapor of ethyl alcohol to reaction with steam at a temperature between 475 and 485 C. in presence of a catalyst composed of zinc oxide and calcium silicate.
- Process for the manufacture of acetone which comprises subjecting a mixture of between 2 and 10 volumes of steam and 1 volume of ethyl alcohol vapor to reaction with a catalyst composed of zinc oxide and calcium silicate at a temperature between 475 and 485 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
l atented July 3, 193 3 MANUFACTURE OF OXYGEN-CONTAINING ALIPHATEC COMPGUNDS Henry Dreyfus, London, England No Drawing.
Appiication October 30, 1930, Serial No. 492,361. In Great Britain November 28,
18 Claims.
This invention relates to the production of ketones from aliphatic primary alcohols containing at least two carbon atoms, and especially to the production of acetone from ethyl alcohol.
According to the invention I have found that aliphatic ketones may be prepared in a highly satisfactory manner, by subjecting the vapors of the primary aliphatic alcohols, in admixture with water vapor, to the action of high or relatively high temperatures in the presence or" a catalyst mass comprising zinc, i. e. a catalyst mass containing zinc and/or one or more salts or compounds of zinc. The catalyst or catalyst mass may also advantageously contain one or more alkali or preferably earth alkali oxides, hydroxides or salts, such as carbonates or other salts and especially salts of the weaker acids, such for instance as silicates or borates.
By means or the invention acetone can readily be produced from ethyl alcohol and homologous ketones can be produced from the homologous alcohols, e. g. diethyl ketone can readily be produced from propyl alcohol.
As examples of catalysts suitable for use in performing the invention may be mentioned metallic zinc, zinc acetate, zinc oxide, zinc carbon-- ate; mixtures of two or more of such bodies; one or more of such bodies in admixture or association with one or more oxides, hydroxides or salts (e. g. carbonates, borates, silicates) of calcium, barium, magnesium or other earth alkali metals.
The catalysts may, ii desired, be employed spread upon or deposited upon filling or contact materials, such for instance as pumice, kieselguhr or the like.
The reaction of the invention may be performed at temperatures between about 200 700 C. and especially at temperatures between about 400-550" C. The reaction may be performed at any desired pressure whether higher or lower than normal atmospheric, for instance under reduced pressure or vacuum, or under higher pressures, such for instance as 3-10 atmospheres or more.
For the purposes of the invention I preferably employ mixtures of the alcohol vapor and steam containing relatively large amounts of steam or water vapor, e. g. amounts such as 2-10 or more times 'the volume of the alcohol vapor present. I may also mix with the alcohol vapor and water vapor, oxygen or a gaseous mixture containing the same, such for instance as air. For instance, I may mix oxygen or a gas containing the same 55 in a relatively large amount, such for instance as 25 times or more the volume of the alcohol vapor present, though it is, of course, to be understood that I may employ smaller quantities of such gases or operate in the absence of such gases. If desired, the mixture of alcohol vapor and water vapor, whether or not such mixture contains oxygen or a gas containing the same, may contain indifferent gases such for instance as nitrogen, carbon dioxide and the like. The mixture or" the alcohol vapor and water vapor, containing or not containing the gases or gaseous mixtures such as aforesaid, may be submitted to the reaction in any convenient way, as for instance the mixture may be passed in a rapid stream through a tube or other form of '7 apparatus (e. g. a tube or apparatus of copper, iron, staybrite, earthenware, or the like) filled or provided with a catalyst and heated to the desired temperature.
The following example serves to illustrate a convenient form of operation of the invention, but it is to be understood that the invention is in no way limited thereto.
Example A mixture of ethyl alcohol steam and oxygen in the proportions of 1:511 by volume is passed in a rapid stream over or in contact with the catalyst contained in a tube (e. g. of copper) and 'naintained at a temperature of between about 4'75 and 485 C. The catalyst is composed of zinc acetate or of zinc oxide and calcium silicate, e. g. a mixture of two molecular proportions of zinc oxide with one molecular proportion of calcium silicate.
The resulting acetone can, if desired, be purifled by frictional distillation.
What I claim and desire to secure by Letters Patent is 1, Process for the manufacture of an aliphatic ketone, which comprises subjecting the vapor of a primary aliphatic alcohol containing at least two carbon atoms to reaction with steam at an elevated temperature in presence or" a catalyst mass comprising essentially zinc and which is free from other heavy metals.
2. Process for the manufacture of an aliphatic ketone, which comprises subjecting the vapor of a primary aliphatic alcohol containing at least two carbon atoms to reaction with steam at an elevated temperature in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
3. Process for the manufacture of an aliphatic of a catalyst mass comprising essentially zinc and.
which is free from other heavy metals.
5. Process for the manufacture of an aliphatic ketone, which comprises subjecting the vapor of a primary aliphatic alcohol containing at least two carbon atoms to reactionwith steam at a temperature between 200 and 700 C. in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
6. Process for the manufacture of an aliphatic ketone, which comprises subjecting a mixture of between 2 and 10 volumes of steam and 1 volume of the vapor of a primary aliphatic alcohol containing at least two carbon atoms to reaction at an elevated temperature in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
7. Process for the manufacture of acetone, which comprises subjecting the vapor of ethyl alcohol to reaction with steam at an elevated temperature in presence of a catalyst mass comprising essentially zinc and which is free from other heavy metals.
8. Process for the manufacture of acetone, which comprises subjecting the vapor of ethyl alcohol to reaction with steam at an elevated temperature in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
9. Process for the manufacture of diethyl ketone, which comprises subjecting the vapor of propyl alcohol to reaction with steam at an elevated temperature in presence of a catalyst mass comprising essentially zinc.
10. Process for the manufacture of acetone, which comprises subjecting the vapor of ethyl alcohol to reaction with steam at a temperature between 200 and 700 C. in presence of a catalyst mass consisting of at least one substance selected from the group consisting of metallic zinc and compounds of zinc.
11. Process for the manufacture ofacetone, which comprises subjecting the vapor of ethyl alcohol to reaction with steam at a temperature between 400 and 550 C in presence of a catalyst mass comprising essentially a. compound of zinc and a compound of an earth alkali metal.
12. Process for the manufacture of acetone, which comprises subjecting a mixture of between 2 and 10 volumes of steam and 1 volume of ethyl alcohol vapor to reaction at a temperature between 400 and 550 C. in presence of a catalyst mass comprising essentially a compound of zinc and a compound of an earth alkali metal.
13. Process for the manufacture of diethyl ketone, which comprises subjecting the vapor of propyl alcohol to reaction with steam at a temperature between 200 and 700 C. in presence of a catalyst mass comprising essentialy Zinc.
14. Process for the manufacture of diethyl ketone, which comprises subjecting the vapor of propyl alcohol to reaction with steam at a temperature between 400 and 550 C. in presence of a catalyst mass comprising essentially a compound of zinc and a compound of an earth alkali metal.
15. Process for the manufacture of diethyl ketone, which comprises subjecting a mixture of between 2 and 10 volumes of steam and 1 volume of propyl alcohol vapor to reaction at a tel perature between 400 and 550 C. in presence of a catalyst mass comprising essentially a compound of zinc and a compound of an earth alkali metal.
16. Process for the manufacture or" acetone, which comprises subjecting the vapor of ethyl alcohol to reaction with steam at a temperature between 400 and 550 C. in presence of a catalyst composed of zinc oxide and a compound of an earth alkali metal.
17. Process for the manufacture of acetone, which comprises subjecting the vapor of ethyl alcohol to reaction with steam at a temperature between 475 and 485 C. in presence of a catalyst composed of zinc oxide and calcium silicate.
18. Process for the manufacture of acetone, which comprises subjecting a mixture of between 2 and 10 volumes of steam and 1 volume of ethyl alcohol vapor to reaction with a catalyst composed of zinc oxide and calcium silicate at a temperature between 475 and 485 C.
HENRY DREYFU S.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1965072X | 1929-11-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1965072A true US1965072A (en) | 1934-07-03 |
Family
ID=10894788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US492361A Expired - Lifetime US1965072A (en) | 1929-11-28 | 1930-10-30 | Manufacture of oxygen-containing aliphatic compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1965072A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2549844A (en) * | 1948-08-23 | 1951-04-24 | Standard Oil Dev Co | Dehydrogenation catalyst |
-
1930
- 1930-10-30 US US492361A patent/US1965072A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2549844A (en) * | 1948-08-23 | 1951-04-24 | Standard Oil Dev Co | Dehydrogenation catalyst |
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